The comprehensive fundraising handbook for startup founders.

With input from over 60 entrepreneurs, investors, and legal experts, this in-depth resource is your companion as an entrepreneur. Filled with practical pitching advice, term sheet details, real-world scenarios, and pitfalls to avoid.

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Length: 310 pages
Edition: e1.1.2
Last Updated: 2021-06-14
Language: English
ISBN (print):
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Founders shouldn’t have to figure fundraising out the hard way when they can learn from those who have already been through the process. The Holloway Guide to Raising Venture Capital is full of practical advice that will be helpful to any entrepreneur.Brad Feld(Foundry Group)

Everyone should have access to expert knowledge.

Venture capital is a powerful tool for entrepreneurship—one that can help overcome some of the numerous challenges of starting and scaling a new business. But the path of deciding if, when, and how to raise early-stage venture capital is navigated most easily by those with past experience, insider knowledge, and the right connections. It’s notoriously easy for founders to take wrong turns in their path to successfully finance a company.

The lead author of this Guide, Andy Sparks, raised $17M for his last startup—having failed to secure any funding for his first company. He’d moved to Silicon Valley without a network, and spent the next four years piecing together how fundraising works, from hundreds of conversations, countless hours of internet searches, and multiple $900 sessions with lawyers.

Learning how to fundraise doesn’t have to be so painful—or so costly. Anyone aspiring to build a company should have access to the experiences and knowledge of those who have gone before. We’ve pulled together 40 experts—lawyers, founders, and investors—to build a practical Guide that helps founders approach the process with confidence.


I wish this resource had existed back when I was a CEO raising money from VCs. In my work today as a seed investor, I share with my portfolio founders a lot of the knowledge gathered in this Guide. Now that this definitive resource exists, I'm going to send it to every founder I work with!Rafael Corrales(Background Capital)
Raising venture capital is a huge decision for founders. I highly recommend this Holloway Guide—it dives deep into how to raise, but also gives an honest assessment of why founders should or shouldn’t raise VC and the alternative paths for building companies.Tyler Tringas(Earnest Capital)
Venture funding of startups is a secretive process that has typically required insider knowledge to navigate well. This new Holloway Guide pulls back the curtain and shares everything you need to know as a new founder raising money for the first time. I wish I had access to this kind of knowledge when I was getting started; it would have saved me years of hard lessons.Sean Byrnes(CEO at Outlier and former CTO at Flurry)
Holloway has taken a thoughtful, non-biased approach putting together this comprehensive Guide to raising venture capital. Rather than being a mile wide and an inch deep like other material out there, they have focused on context and quality.Zach Klempf(CEO, Selly Automotive)
We need more startups. But many never get the funding they need to fulfill their true potential. This Guide is designed to empower founders with the insights and strategies to find investors that share the same convictions as the founders themselves.Ryan Hoover(founder of ProductHunt and investor at Weekend Fund)
Holloway has brought a digestible and actionable first-class experience to a very intimidating topic. The clarity that this Guide offers will leave you with answers, not headaches. If you plan on raising, I can confidently say that this is the only resource you need to read.Jared Erondu(Earnest Capital)

Table of Contents

Part I
The Landscape
Assessing Whether to Raise
Determining When to Raise
Bias and Discrimination in Fundraising
Part II
Choosing a Financing Structure
Part III
Sourcing and Pitching
Designing Your Pitch
Getting the Meeting
Investor Meetings
Part IV
Term Sheets
Essential Terms
Other Terms
Sample Term Sheets
After the Term Sheet
Appendix B: Returns, Management Fees, and Carried Interest
Appendix C: Example Fundraising Pitch Decks
Though it’s getting better, venture capital has traditionally been a fairly closed, blackbox field. This Guide democratizes and demystifies the VC ecosystem, which is an important step toward building a more diverse and inclusive industry.Lindsay Knight(Chicago Ventures)

Researched, written, and edited by experts.

Written by practitioners. Edited by professionals.

Original Author
Andy Sparks
Contributing Authors
Rachel Jepsen
Contribution and Review
José Ancer (Egan Nelson LLP)
Michael Brown (Fenwick & West)
Brad Feld (Foundry Group)
Chris Field (Clerky)
Eric Friedman (Building the Machine)
Alexander Graebe (HyperTrack)
Chris Harvey (Harvey Esquire)
Lindsay Knight (Chicago Ventures)
Craig Montuori (Global EIR)
Danielle Morrill (GitLab)
Leo Polovets (Susa Ventures)
Camille Ricketts (First Round, Notion)
Joe Sadusky (The Wordsmith)
Santosh Sankar (Dynamo Venture Capital)
Aaron Schwartz (Passport Shipping)
Tess Townsend (Journalists in Classrooms)
Tyler Tringas (Earnest Capital)
Joe Wallin (Carney Bradley Spellman)
Eugene Wan (The Engine)
Darby Wong (Clerky)
Haley AndersonResearch and definitions
Hope HackettSwiss Army knife
Rachel JepsenEditor
Joshua LevyEditor
Sakhi MacMillanCopyeditor
Courtney NashEditor
Andy SparksEditor
Dmitriy Kharchenko & Leigh TaylorGraphics
And 28 more

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We believe the reading experience for book-length resources can go beyond paper or e-books. Reading on Holloway means a distraction-free, interactive format to help you find what you need, when you need it, in your browser. Digital access to a Guide also means access to ongoing new content, curated commentary from experts and readers, and features like search and bookmarks.

Screenshot of the guide on phone and laptop

Over 120 definitions of key terms

Definition Product-market fit (product/market fit or PMF) refers to the notion that there is a point at which a given market responds so positively to a company’s product that the product “fits” the market’s needs. A precise point at which “fit” has been achieved does not exist. Instead, product-market fit represents a continuum of traction that ranges from absolute clarity that a company does not have product-market fit to maybe they have product-market fit to experts disagree whether they have product-market fit all the way to it’s beyond all doubt they have product-market fit.

Find what you want, when you need it

Shadow preferred stock
Preferred stock
Preferred stock vs. common stock
Assessing Whether to Raise
usually means agreeing to protective provisions for preferred stockholders or giving up a board seat

Pitfalls and confusions highlighted

danger️️ Even if you’ve negotiated a cap on the portion of your investors’ legal fees you’re responsible for covering, your counsel’s fees can get out of control if you aren’t careful. If your lawyers are arguing about anything meaningful, you should tell them to bring it to you before it goes back and forth between different legal teams more than once.

confusion Not everyone has embraced the pre-seed term, which some consider overly specific and constraining. Until recently, a company’s earliest institutional investors were simply called seed stage firms. Some firms that consider themselves seed-stage will invest pre-product, all the way up to the last check before a Series A round.

controversy A warm intro from a close friend or colleague never hurts.* But not everyone agrees you need to be close with the person making the intro. So long as the introduction is credible, it can be a good start, even if it’s not necessarily an endorsement.*

Visual presentations

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The Holloway Guide to VC is an incredibly well-curated resource that’s easily searchable and is heavily grounded in first principles. I wish I’d had this guide when trying to raise VC money for my first startup!Kiren Srinivasan(Holberton School)

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At Holloway, we imagine a place on the web where depth, quality, and high-value writing are the norm. A place where experts’ ideas are accessible to anyone. Where thoughtful, inclusive, and well-written resources win over quick takes, self-promoting blog posts, and content marketing.

We believe you, the reader, know the difference. It’s 2021. You recognize sites riddled with ads and clickbait headlines. Deep and comprehensive resources take expertise, time, and money to build. By buying access to this title, you’re supporting a place online that makes longform reading a pleasure—and allowing us to pay authors, contributors, engineers, and editors who build and improve them. Holloway is a new and powerful way to publish. We hope you’ll join us on the journey.

Does this sound like you?

  • I just got off the phone with my lawyer about my term sheet, and still feel confused about what participating preferred and full ratchet mean. I wish this stuff were just written down.
  • What’s the difference between a managing director, partner, venture partner, principal, associate, or an analyst in a VC firm? Who should I be talking to?
  • We aren’t in a standard tech hub like Silicon Valley or New York City, and don’t know any investors. Where do we even start?
  • I’ve read blog posts about founders deciding against raising venture capital. How do I know whether raising venture capital is a good idea for my business?

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